Sodium Carbonate → 5-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidine

HRID 12690

반응식

HRID 12690 반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.I[C:15]1[O:19][C:18]([CH3:20])=[N:17][C:16]=1[CH3:21].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:20][C:18]1[O:19][C:15]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[C:16]([CH3:21])[N:17]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 593375895-Iodo-2,4-dimethyl-oxazole

생성물 1

HCID 589942085-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidine수율 67.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

2,4-Dimethoxy-pyrimidine-5-boronic acid (840 mg, 4.6 mmol) was dissolved in degassed n-PrOH (40 mL) and then 5-iodo-2,4-dimethyl-oxazole (Prep60, 850 mg, 3.8 mmol), Na2CO3 (848 mg, 8 mmol), PPh3 (332 mg, 1.3 mmol) and Pd(OAc)2 (85 mg, 0.38 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by SCX cartridge to give 600 mg of the title compound (66% yield).

후처리

  1. temperatureat reflux for 4 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by SCX cartridge

출처 및 근거

ORD 기록
ord-49aa7eb002944783b9f978f9c7b080b9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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